Structural analysis and anti-complement activity of polysaccharides extracted from Grateloupia livida (Harv.) Yamada
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摘要
Polysaccharides were extracted from Grateloupia livida(Harv.) Yamada using hot water(extracted product denoted WGW) and then degraded in dilute sulfuric acid(degraded product denoted WGWD). The degraded mixture was then separated into four fractions through anion exchange chromatography on 2-diethylaminoethanol(DEAE)-Bio-Gel Agarose FF gel. Electrospray ionization collision-induced dissociation tandem mass spectrometry(ESI-CID-MS/MS) was performed to elucidate the structural features of all fractions. In combination with nuclear magnetic resonance spectroscopy(NMR)and infrared spectroscopy(IR) data, the major polysaccharide structures were concluded to be μ-carrageenan and κ-carrageenan. μ-Carrageenan usually has a backbone of alternating 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-galactopyranose residues sulfated at C-6, while κ-carrageenan consists of alternating 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-3,6-anhydrogalactopyranose residues. Trace v-carrageenan, composed of 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-galactopyranose residues sulfated at C-2 and C-6, was also detected. Furthermore, the polysaccharide had a backbone comprising 1,3-linked β-D-galactopyranose and1,4-linked α-L-galactopyranose sulfated at C-6, which is the agarose precursor. The hydroxy groups in the galactopyranose were partially substituted by methyl and pyruvic acid acetal(PA) groups. The anticomplementary activities of WGW and its derivatives against classical pathways were measured. The native polysaccharides in WGW had higher activities, while the derivatives had much weaker activities. This indicated that the molecular weight and sulfate content were important factors affecting the anti-complement activity.
Polysaccharides were extracted from Grateloupia livida(Harv.) Yamada using hot water(extracted product denoted WGW) and then degraded in dilute sulfuric acid(degraded product denoted WGWD). The degraded mixture was then separated into four fractions through anion exchange chromatography on 2-diethylaminoethanol(DEAE)-Bio-Gel Agarose FF gel. Electrospray ionization collision-induced dissociation tandem mass spectrometry(ESI-CID-MS/MS) was performed to elucidate the structural features of all fractions. In combination with nuclear magnetic resonance spectroscopy(NMR)and infrared spectroscopy(IR) data, the major polysaccharide structures were concluded to be μ-carrageenan and κ-carrageenan. μ-Carrageenan usually has a backbone of alternating 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-galactopyranose residues sulfated at C-6, while κ-carrageenan consists of alternating 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-3,6-anhydrogalactopyranose residues. Trace v-carrageenan, composed of 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-galactopyranose residues sulfated at C-2 and C-6, was also detected. Furthermore, the polysaccharide had a backbone comprising 1,3-linked β-D-galactopyranose and1,4-linked α-L-galactopyranose sulfated at C-6, which is the agarose precursor. The hydroxy groups in the galactopyranose were partially substituted by methyl and pyruvic acid acetal(PA) groups. The anticomplementary activities of WGW and its derivatives against classical pathways were measured. The native polysaccharides in WGW had higher activities, while the derivatives had much weaker activities. This indicated that the molecular weight and sulfate content were important factors affecting the anti-complement activity.
Polysaccharides were extracted from Grateloupia livida(Harv.) Yamada using hot water(extracted product denoted WGW) and then degraded in dilute sulfuric acid(degraded product denoted WGWD). The degraded mixture was then separated into four fractions through anion exchange chromatography on 2-diethylaminoethanol(DEAE)-Bio-Gel Agarose FF gel. Electrospray ionization collision-induced dissociation tandem mass spectrometry(ESI-CID-MS/MS) was performed to elucidate the structural features of all fractions. In combination with nuclear magnetic resonance spectroscopy(NMR)and infrared spectroscopy(IR) data, the major polysaccharide structures were concluded to be μ-carrageenan and κ-carrageenan. μ-Carrageenan usually has a backbone of alternating 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-galactopyranose residues sulfated at C-6, while κ-carrageenan consists of alternating 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-3,6-anhydrogalactopyranose residues. Trace v-carrageenan, composed of 1,3-linked β-D-galactopyranose residues sulfated at C-4 and 1,4-linked a-D-galactopyranose residues sulfated at C-2 and C-6, was also detected. Furthermore, the polysaccharide had a backbone comprising 1,3-linked β-D-galactopyranose and1,4-linked α-L-galactopyranose sulfated at C-6, which is the agarose precursor. The hydroxy groups in the galactopyranose were partially substituted by methyl and pyruvic acid acetal(PA) groups. The anticomplementary activities of WGW and its derivatives against classical pathways were measured. The native polysaccharides in WGW had higher activities, while the derivatives had much weaker activities. This indicated that the molecular weight and sulfate content were important factors affecting the anti-complement activity.
引文
Chen M M,Wu J J,Shi S S,Chen Y L,Wang H J,Fan H W,Wang S C. 2016. Structure analysis of a heteropolysaccharide from Taraxacum mongolicum Hand.-Mazz. and anticomplementary activity of its sulfated derivatives. Carbohydrate Polymers,152:241-252.
De Souza M C R, Marques C T, Dore C M G, Da Silva F R F,Rocha H A O, Leite E L. 2007. Antioxidant activities of sulfated polysaccharides from brown and red seaweeds.Journal of Applied Phycology, 19(2):153-160.
DuBois M, Gilles K A, Hamilton J K, Rebers P A, Smith F.1956. Colorimetric method for determination of sugars and related substances. Analytical Chemistry, 28(3):350-356.
Duckworth M, Yaphe W. 1971. The structure of agar:part I.Fractionation of a complex mixture of polysaccharides.Carbohydrate Research, 16(1):189-197.
Falshaw R, Fumeaux R H. 1998. Structural analysis of carrageenans from the tetrasporic stages of the red algae,Gigartina lanceata and Gigartina chapmanii(Gigartinaceae, Rhodophyta). Carbohydrate Research,307(3-4):325-331.
Ji M H. 1997. Seaweed Chemistry. Science Press, Beijing,China. p.69-70, 143-164.(in Chinese)
Jiang Z B, Chen Y C, Yao F, Chen W Z, Zhong S P, Zheng F C,Shi G G. 2013. Antioxidant, antibacterial and antischistosomal activities of extracts from Grateloupia livida(Harv.)Yamada. PLoS One, 8(11):e80413.
Jiao G L, Yu G L, Zhang J Z, Ewart H S. 2011. Chemical structures and bioactivities of sulfated polysaccharides from marine algae. Marine Drugs, 9(2):196-223.
Jin W H, Guo Z M, Wang J, Zhang W J, Zhang Q B. 2013a.Structural analysis of sulfated fucan from Saccharina japonica by electrospray ionization tandem mass spectrometry. Carbohydrate Research, 369:63-67.
Jin W H, Zhang W J, Liang H Z, Zhang Q B. 2016. The structure-activity relationship between marine algae polysaccharides and anti-complement activity. Marine Drugs, 14(1):3.
Jin W H, Zhang W J, Wang J, Ren S M, Song N, Zhang Q B.2013b. Structural analysis of heteropolysaccharide from Saccharina japonica and its derived oligosaccharides.International Journal of Biological Macromolecules, 62:697-704.
Kawai Y, Seno N, Anno K, 1969, A modified method for chondrosulfatase assay. Analytical Biochemistry, 32(2):314-321.
Knutsen S H, Grasdalen H. 1992a. Analysis of carrageenans by enzymic degradation, gel filtration and'H NMR spectroscopy. Carbohydrate Polymers, 19(3):199-210.
Knutsen S H, Grasdalen H. 1992b. The use of neocarrabiose oligosaccharides with different length and sulphate substitution as model compounds for'H-NMR spectroscopy. Carbohydrate Research, 229(2):233-244.
Lins K O A L, Bezerra D P, Alves A P N N, Alencar N M N,Lima M W, Torres V M, Farias W R L, Pessoa C, De Moraes M O, Costa-Lotufo L V. 2009. Antitumor properties of a sulfated polysaccharide from the red seaweed Champia feldmannii(Diaz-Pifferer). Journal of Applied Toxicology, 29(1):20-26.
Liu F, Pang S J. 2010. Stress tolerance and antioxidant enzymatic activities in the metabolisms of the reactive oxygen species in two intertidal red algae Grateloupia turuturu and Palmaria palmata. Journal of Experimental Marine Biology and Ecology, 382(2):82-87.
Maslen S, Sadowski P, Adam A, Lilly K, Stephens E. 2006.Differentiation of isomeric N-glycan structures by normalphase liquid chromatography-MALDI-TOF/TOF tandem mass spectrometry. Analytical Chemistry, 78(24):8 491-8 498.
Neushul M. 1990. Antiviral carbohydrates from marine red algae. Hydrobiologia, 204(1):99-104.
Ngo D H, Kim S K. 2013. Sulfated polysaccharides as bioactive agents from marine algae. International Journal of Biological Macromolecules, 62:70-75.
Shanmugam M, Mody K H. 2000. Heparinoid-active sulphated polysaccharides from marine algae as potential blood anticoagulant agents. Current Science, 79(12):1 672-1 683.
Usov A I. 1984. NMR spectroscopy of red seaweed polysaccharides:agars, carrageenans, and xylans.Botanica Marina, 27(5):189-202.
Usov A I.1998. Structural analysis of red seaweed galactans of agar and carrageenan groups. Food Hydrocolloids, 12(3):301-308.
Wang S C, Bligh S W A, Shi S S, Wang Z T, Hu Z B, Crowder J,Branford-White C,Vella C. 2007. Structural features and anti-HIV-1 activity of novel polysaccharides from red algae Grateloupia longifolia and Grateloupia filicina.International Journal of Biological Macromolecules,41(4):369-375.
Xu H, Zhang Y Y, Zhang J W, Chen D F. 2007. Isolation and characterization of an anti-complementary polysaccharide D3-S1 from the roots of Bupleurum smithii. International Immunopharmacology,7(2):175-182.
Yaphe W, Arsenault G P. 1965. Improved resorcinol reagent for the determination of fructose, and of 3,6-anhydrogalactose in polysaccharides. Analytical Biochemistry, 13(1):143-148.
Zaia J, Li X Q, Chan S Y, Costello C E. 2003. Tandem mass spectrometric strategies for determination of sulfation positions and uronic acid epimerization in chondroitin sulfate oligosaccharides. Journal of the American Society for Mass Spectrometry, 14(11):1 270-1 281.
Zhang Q B, Yu P Z, Li Z E, Zhang H, Xu Z H, Li P C. 2003.Antioxidant activities of sulfated polysaccharide fractions from Porphyra haitanesis. Journal of Applied Phycology,15(4):305-310.
Zhang W J, Jin W H, Sun D L, Zhao L Y, Wang J, Duan D L,Zhang Q B. 2015. Structural analysis and anti-complement activity of polysaccharides from Kjellmaniella crsaaifolia.Marine Drugs, 13(3):1 360-1 374.
De Souza M C R, Marques C T, Dore C M G, Da Silva F R F,Rocha H A O, Leite E L. 2007. Antioxidant activities of sulfated polysaccharides from brown and red seaweeds.Journal of Applied Phycology, 19(2):153-160.
DuBois M, Gilles K A, Hamilton J K, Rebers P A, Smith F.1956. Colorimetric method for determination of sugars and related substances. Analytical Chemistry, 28(3):350-356.
Duckworth M, Yaphe W. 1971. The structure of agar:part I.Fractionation of a complex mixture of polysaccharides.Carbohydrate Research, 16(1):189-197.
Falshaw R, Fumeaux R H. 1998. Structural analysis of carrageenans from the tetrasporic stages of the red algae,Gigartina lanceata and Gigartina chapmanii(Gigartinaceae, Rhodophyta). Carbohydrate Research,307(3-4):325-331.
Ji M H. 1997. Seaweed Chemistry. Science Press, Beijing,China. p.69-70, 143-164.(in Chinese)
Jiang Z B, Chen Y C, Yao F, Chen W Z, Zhong S P, Zheng F C,Shi G G. 2013. Antioxidant, antibacterial and antischistosomal activities of extracts from Grateloupia livida(Harv.)Yamada. PLoS One, 8(11):e80413.
Jiao G L, Yu G L, Zhang J Z, Ewart H S. 2011. Chemical structures and bioactivities of sulfated polysaccharides from marine algae. Marine Drugs, 9(2):196-223.
Jin W H, Guo Z M, Wang J, Zhang W J, Zhang Q B. 2013a.Structural analysis of sulfated fucan from Saccharina japonica by electrospray ionization tandem mass spectrometry. Carbohydrate Research, 369:63-67.
Jin W H, Zhang W J, Liang H Z, Zhang Q B. 2016. The structure-activity relationship between marine algae polysaccharides and anti-complement activity. Marine Drugs, 14(1):3.
Jin W H, Zhang W J, Wang J, Ren S M, Song N, Zhang Q B.2013b. Structural analysis of heteropolysaccharide from Saccharina japonica and its derived oligosaccharides.International Journal of Biological Macromolecules, 62:697-704.
Kawai Y, Seno N, Anno K, 1969, A modified method for chondrosulfatase assay. Analytical Biochemistry, 32(2):314-321.
Knutsen S H, Grasdalen H. 1992a. Analysis of carrageenans by enzymic degradation, gel filtration and'H NMR spectroscopy. Carbohydrate Polymers, 19(3):199-210.
Knutsen S H, Grasdalen H. 1992b. The use of neocarrabiose oligosaccharides with different length and sulphate substitution as model compounds for'H-NMR spectroscopy. Carbohydrate Research, 229(2):233-244.
Lins K O A L, Bezerra D P, Alves A P N N, Alencar N M N,Lima M W, Torres V M, Farias W R L, Pessoa C, De Moraes M O, Costa-Lotufo L V. 2009. Antitumor properties of a sulfated polysaccharide from the red seaweed Champia feldmannii(Diaz-Pifferer). Journal of Applied Toxicology, 29(1):20-26.
Liu F, Pang S J. 2010. Stress tolerance and antioxidant enzymatic activities in the metabolisms of the reactive oxygen species in two intertidal red algae Grateloupia turuturu and Palmaria palmata. Journal of Experimental Marine Biology and Ecology, 382(2):82-87.
Maslen S, Sadowski P, Adam A, Lilly K, Stephens E. 2006.Differentiation of isomeric N-glycan structures by normalphase liquid chromatography-MALDI-TOF/TOF tandem mass spectrometry. Analytical Chemistry, 78(24):8 491-8 498.
Neushul M. 1990. Antiviral carbohydrates from marine red algae. Hydrobiologia, 204(1):99-104.
Ngo D H, Kim S K. 2013. Sulfated polysaccharides as bioactive agents from marine algae. International Journal of Biological Macromolecules, 62:70-75.
Shanmugam M, Mody K H. 2000. Heparinoid-active sulphated polysaccharides from marine algae as potential blood anticoagulant agents. Current Science, 79(12):1 672-1 683.
Usov A I. 1984. NMR spectroscopy of red seaweed polysaccharides:agars, carrageenans, and xylans.Botanica Marina, 27(5):189-202.
Usov A I.1998. Structural analysis of red seaweed galactans of agar and carrageenan groups. Food Hydrocolloids, 12(3):301-308.
Wang S C, Bligh S W A, Shi S S, Wang Z T, Hu Z B, Crowder J,Branford-White C,Vella C. 2007. Structural features and anti-HIV-1 activity of novel polysaccharides from red algae Grateloupia longifolia and Grateloupia filicina.International Journal of Biological Macromolecules,41(4):369-375.
Xu H, Zhang Y Y, Zhang J W, Chen D F. 2007. Isolation and characterization of an anti-complementary polysaccharide D3-S1 from the roots of Bupleurum smithii. International Immunopharmacology,7(2):175-182.
Yaphe W, Arsenault G P. 1965. Improved resorcinol reagent for the determination of fructose, and of 3,6-anhydrogalactose in polysaccharides. Analytical Biochemistry, 13(1):143-148.
Zaia J, Li X Q, Chan S Y, Costello C E. 2003. Tandem mass spectrometric strategies for determination of sulfation positions and uronic acid epimerization in chondroitin sulfate oligosaccharides. Journal of the American Society for Mass Spectrometry, 14(11):1 270-1 281.
Zhang Q B, Yu P Z, Li Z E, Zhang H, Xu Z H, Li P C. 2003.Antioxidant activities of sulfated polysaccharide fractions from Porphyra haitanesis. Journal of Applied Phycology,15(4):305-310.
Zhang W J, Jin W H, Sun D L, Zhao L Y, Wang J, Duan D L,Zhang Q B. 2015. Structural analysis and anti-complement activity of polysaccharides from Kjellmaniella crsaaifolia.Marine Drugs, 13(3):1 360-1 374.